research communications
N′-(4-nitrobenzylidene)benzohydrazide: a new hydrazone derivative
of 4-[(4-methylbenzyl)oxy]-aDepartment of Chemistry, Rajshahi University, Rajshahi-6205, Bangladesh, bDepartment of Applied Science, Faculty of Science, Okayama University of Science, Japan, cCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan, and dDepartment of Chemical and Pharmaceutical Sciences, University of Trieste, Italy
*Correspondence e-mail: s1510923194@ru.ac.bd
The molecular structure of the title compound, C22H19N3O4, shows a non-coplanar conformation, with dihedral angles between the phenyl rings of 73.3 (1) and 80.9 (1)°. These deformations are induced by the crystal packing that is mainly governed by N—H⋯O and C—H⋯O hydrogen bonds, forming a mono-periodic arrangement parallel to the b axis.
Keywords: crystal structure; hydrazine; hydrazone.
CCDC reference: 2232132
1. Chemical context
et al., 2013). The presence of tautomeric forms facilitates their coordination behavior in neutral or anionic species (Banna et al., 2022) with metal ions (Zülfikaroğlu et al., 2020). The chemical diversity and pharmacological accessibility of hydrazone and its derivatives paves the way for research exploring drug design and discovery (Verma et al., 2014).
are a special class of which can be obtained by condensation between an alkyl or aryl hydrazine and a carbonyl compound (aldehyde or ketone). The active pharmacophore group, —CH=N—NH—C=O—, present in a hydrazone is primarily responsible for its broad spectrum of biological aspects (TahaIn this context and in a continuation of our recent work (Banna et al., 2023), we report here on the synthesis and crystal-structure determination of another derivatized aroylhydrazone bearing an ether group.
2. Structural commentary
The molecular structure of the hydrazone compound is shown in Fig. 1. The acyl–hydrazone (—CH=N—NH—C=O—) group connects the p-nitrophenyl group and the central phenyl ring, which in turn is bound to the p-methylbenzyloxy fragment. An E-configuration is observed with respect to the double bond of the hydrazone bridge N2=C16. The N1—N2 bond length of 1.376 (4) Å is slightly shorter than that of 1.397 (4) Å determined in the corresponding derivative having a thienyl ring replacing the p-nitrophenyl group (Banna et al., 2023). On the other hand, the O2=C15 bond of 1.237 (4) Å is close to that determined in the thienyl derivative [1.236 (4) Å], and typical of a ketonic linkage, while an equilibrium between the keto and enol forms is present in solution. The nitrophenyl group and the benzohydrazone fragment form a dihedral angle of 73.3 (1)° while the terminal 4-methylbenzyl group is rotated by 80.9 (1)° with respect to the central phenyl ring.
Fig. 2 depicts a superimposition of the molecular structure of the title compound with the thienyl derivative (Banna et al., 2023). It is worth noting the different orientations of the carbohydrazide CO—NH—N moiety, likely induced by crystal-packing requirements.
3. Supramolecular features
The crystal packing is governed by hydrogen-bonding interactions (Table 1, with corresponding symmetry codes) realized between the imino group N1—H1 with carbonyl oxygen atom O2ii of a symmetry-related molecule. This results in a mono-periodic arrangement parallel to the b axis. In addition, non-classical C16—H16⋯O2ii hydrogen bonds between a methine group and the carbonyl O atom and C21—H21⋯O4iii between an aromatic C—H group and one of the nitro O atoms are also present, as shown in Fig. 3. The ribbons are further connected by C14—H14⋯N2i interactions (Table 1). No significant π-stacking interaction is found in the crystal (all centroid-to-centroid distances between phenyl rings are > 5.0 Å).
4. Database survey
For a closely related structure with a thienyl moiety, see: Banna et al. (2023); for some other aroylhydrazones, see: Ban & Li (2009); Chantrapromma et al. (2016); Horkaew et al. (2011); Zong & Wu (2013). All these molecules exhibit an E-configuration about the double bond of the hydrazone bridge, and they have comparable bond lengths and angles in the C=N—NH—C moiety, in agreement with the present geometrical parameters. For reference bond-length data, see: Allen et al. (1987).
5. Synthesis and crystallization
The synthesis of the compound follows a procedure previously described (Banna et al., 2023). To a solution of 4-[(4-methylbenzyl)oxy]benzoylhydrazine (0.25 g, 0.97 mmol in 20 ml of absolute ethanol), a solution of 4-nitrobenzaldehyde (0.14 g, 0.97 mmol) in 5 ml ethanol was added and the mixture was heated and refluxed for 2 h. A colorless precipitate was obtained, filtered off, and washed several times with hot ethanol to eliminate any types of starting materials prior to being dried in a desiccator. The title compound was recrystallized from a mixture of DMF and ethanol. Colorless crystals suitable for X-ray diffraction were obtained after 60 d of keeping the sample solution undisturbed.
Yield: 0.29 g, 79%; melting point (m.p.): 531–533 K; FT–IR: 1636 ν(C=Oamide), 3315 ν(N—H), 1606 ν(C=Nazomethine). LC–MS (FAB) m/z: [M + H]+ calculated for C22H19N3O4; 390.1446; found 390.1448.
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms were placed at geometrical positions, except for the N—H hydrogen atom, the position of which was located in a difference-Fourier map and freely refined. The of −0.8 (9) indicates that the cannot confidently be derived from the data based on Mo radiation.
details are summarized in Table 2Supporting information
CCDC reference: 2232132
https://doi.org/10.1107/S2056989023003948/wm5682sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003948/wm5682Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023003948/wm5682Isup3.cml
Data collection: RAPID-AUTO (Rigaku, 2018); cell
RAPID-AUTO (Rigaku, 2018); data reduction: RAPID-AUTO (Rigaku, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).C22H19N3O4 | F(000) = 408 |
Mr = 389.40 | Dx = 1.372 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71075 Å |
a = 8.9485 (8) Å | Cell parameters from 5984 reflections |
b = 5.0612 (5) Å | θ = 2.3–27.5° |
c = 20.949 (2) Å | µ = 0.10 mm−1 |
β = 96.585 (7)° | T = 173 K |
V = 942.54 (16) Å3 | Platel, colorless |
Z = 2 | 0.30 × 0.28 × 0.03 mm |
Rigaku R-AXIS RAPID diffractometer | 2635 reflections with I > 2σ(I) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.050 |
ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→11 |
Tmin = 0.749, Tmax = 0.997 | k = −5→6 |
9086 measured reflections | l = −27→27 |
3799 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.0637P)2 + 0.0221P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.126 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.19 e Å−3 |
3799 reflections | Δρmin = −0.16 e Å−3 |
266 parameters | Absolute structure: Flack x determined using 741 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: −0.8 (9) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1477 (3) | 0.5424 (5) | 0.66816 (11) | 0.0476 (7) | |
O2 | 0.3072 (3) | 0.1188 (5) | 0.39878 (10) | 0.0407 (6) | |
O3 | 0.7195 (4) | 0.3955 (11) | 0.04333 (15) | 0.0967 (14) | |
O4 | 0.5966 (4) | 0.7477 (8) | 0.00909 (14) | 0.0786 (10) | |
N1 | 0.3611 (4) | 0.5542 (5) | 0.38830 (13) | 0.0369 (7) | |
H1 | 0.354 (4) | 0.724 (8) | 0.4011 (17) | 0.044* | |
N2 | 0.4173 (3) | 0.5102 (5) | 0.33080 (12) | 0.0359 (7) | |
N3 | 0.6379 (4) | 0.5860 (10) | 0.05105 (16) | 0.0632 (11) | |
C1 | −0.1011 (5) | 0.8823 (12) | 0.93031 (19) | 0.0716 (14) | |
H1A | −0.136189 | 1.063016 | 0.920871 | 0.086* | |
H1B | −0.010078 | 0.886972 | 0.961152 | 0.086* | |
H1C | −0.179652 | 0.782238 | 0.948641 | 0.086* | |
C2 | −0.0660 (4) | 0.7506 (9) | 0.86904 (16) | 0.0472 (10) | |
C3 | 0.0290 (5) | 0.5425 (10) | 0.86983 (18) | 0.0648 (13) | |
H3 | 0.074131 | 0.476727 | 0.909949 | 0.078* | |
C4 | 0.0622 (5) | 0.4232 (10) | 0.81397 (18) | 0.0661 (13) | |
H4 | 0.130000 | 0.278228 | 0.816291 | 0.079* | |
C5 | −0.0019 (4) | 0.5115 (8) | 0.75470 (16) | 0.0401 (8) | |
C6 | −0.0974 (5) | 0.7189 (9) | 0.75353 (18) | 0.0554 (11) | |
H6 | −0.143298 | 0.783136 | 0.713380 | 0.067* | |
C7 | −0.1295 (5) | 0.8387 (11) | 0.80936 (19) | 0.0655 (13) | |
H7 | −0.196585 | 0.984825 | 0.806939 | 0.079* | |
C8 | 0.0349 (4) | 0.3846 (8) | 0.69368 (16) | 0.0462 (9) | |
H8A | 0.072933 | 0.203070 | 0.702463 | 0.055* | |
H8B | −0.056490 | 0.374539 | 0.662284 | 0.055* | |
C9 | 0.1823 (4) | 0.4840 (7) | 0.60809 (15) | 0.0360 (8) | |
C10 | 0.1222 (4) | 0.2735 (7) | 0.57052 (15) | 0.0387 (9) | |
H10 | 0.052049 | 0.156850 | 0.586470 | 0.046* | |
C11 | 0.1652 (4) | 0.2362 (7) | 0.51033 (15) | 0.0382 (8) | |
H11 | 0.123802 | 0.092481 | 0.485007 | 0.046* | |
C12 | 0.2679 (4) | 0.4034 (6) | 0.48530 (15) | 0.0311 (8) | |
C13 | 0.3289 (4) | 0.6103 (7) | 0.52395 (15) | 0.0388 (8) | |
H13 | 0.399403 | 0.727021 | 0.508241 | 0.047* | |
C14 | 0.2876 (4) | 0.6465 (7) | 0.58475 (16) | 0.0419 (9) | |
H14 | 0.332136 | 0.785035 | 0.610979 | 0.050* | |
C15 | 0.3126 (4) | 0.3454 (7) | 0.42105 (15) | 0.0318 (8) | |
C16 | 0.4317 (4) | 0.7143 (7) | 0.29601 (16) | 0.0410 (8) | |
H16 | 0.404496 | 0.884332 | 0.310034 | 0.049* | |
C17 | 0.4910 (4) | 0.6807 (7) | 0.23383 (16) | 0.0405 (9) | |
C18 | 0.5876 (5) | 0.4754 (8) | 0.22322 (18) | 0.0463 (9) | |
H18 | 0.620600 | 0.356662 | 0.257043 | 0.056* | |
C19 | 0.6358 (5) | 0.4437 (9) | 0.16319 (18) | 0.0509 (10) | |
H19 | 0.702781 | 0.304857 | 0.155381 | 0.061* | |
C20 | 0.5843 (4) | 0.6185 (9) | 0.11485 (17) | 0.0491 (10) | |
C21 | 0.4894 (5) | 0.8217 (8) | 0.12357 (17) | 0.0545 (11) | |
H21 | 0.455193 | 0.937239 | 0.089234 | 0.065* | |
C22 | 0.4445 (5) | 0.8546 (8) | 0.18362 (17) | 0.0526 (10) | |
H22 | 0.380496 | 0.998273 | 0.191162 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0515 (15) | 0.0606 (18) | 0.0328 (13) | −0.0128 (14) | 0.0139 (11) | −0.0079 (12) |
O2 | 0.0605 (16) | 0.0307 (12) | 0.0321 (12) | 0.0011 (13) | 0.0101 (11) | −0.0015 (11) |
O3 | 0.076 (2) | 0.168 (4) | 0.0489 (19) | 0.040 (3) | 0.0199 (16) | −0.007 (2) |
O4 | 0.113 (3) | 0.086 (2) | 0.0419 (17) | −0.015 (2) | 0.0324 (17) | 0.0032 (17) |
N1 | 0.0571 (18) | 0.0288 (16) | 0.0259 (14) | 0.0000 (15) | 0.0105 (12) | −0.0017 (12) |
N2 | 0.0492 (17) | 0.0322 (15) | 0.0274 (15) | 0.0007 (14) | 0.0087 (12) | −0.0020 (12) |
N3 | 0.059 (2) | 0.094 (3) | 0.038 (2) | −0.011 (2) | 0.0142 (17) | −0.008 (2) |
C1 | 0.065 (3) | 0.110 (4) | 0.043 (2) | −0.008 (3) | 0.023 (2) | −0.018 (2) |
C2 | 0.0412 (19) | 0.068 (3) | 0.035 (2) | −0.014 (2) | 0.0156 (15) | −0.0043 (19) |
C3 | 0.092 (3) | 0.069 (3) | 0.031 (2) | 0.011 (3) | −0.002 (2) | 0.0080 (19) |
C4 | 0.083 (3) | 0.070 (3) | 0.044 (2) | 0.034 (3) | −0.001 (2) | 0.002 (2) |
C5 | 0.0385 (19) | 0.049 (2) | 0.0337 (18) | −0.0054 (19) | 0.0090 (15) | −0.0003 (16) |
C6 | 0.064 (2) | 0.065 (3) | 0.035 (2) | 0.015 (2) | −0.0024 (18) | 0.0006 (19) |
C7 | 0.055 (2) | 0.094 (4) | 0.046 (2) | 0.025 (3) | 0.0002 (19) | −0.015 (2) |
C8 | 0.048 (2) | 0.056 (2) | 0.037 (2) | −0.008 (2) | 0.0126 (16) | −0.0022 (18) |
C9 | 0.0385 (19) | 0.042 (2) | 0.0282 (17) | 0.0001 (17) | 0.0049 (14) | −0.0003 (15) |
C10 | 0.0410 (19) | 0.037 (2) | 0.0396 (19) | −0.0052 (17) | 0.0121 (16) | −0.0015 (16) |
C11 | 0.0473 (19) | 0.0326 (17) | 0.0349 (19) | −0.0044 (17) | 0.0051 (15) | −0.0069 (15) |
C12 | 0.0395 (19) | 0.0279 (17) | 0.0259 (16) | 0.0045 (16) | 0.0035 (14) | −0.0016 (13) |
C13 | 0.0467 (19) | 0.039 (2) | 0.0311 (17) | −0.0066 (18) | 0.0073 (15) | −0.0001 (16) |
C14 | 0.049 (2) | 0.043 (2) | 0.0333 (19) | −0.0072 (19) | 0.0019 (15) | −0.0074 (16) |
C15 | 0.0373 (19) | 0.0297 (18) | 0.0276 (16) | 0.0041 (16) | 0.0006 (14) | −0.0006 (14) |
C16 | 0.061 (2) | 0.0318 (18) | 0.0320 (18) | −0.0014 (18) | 0.0108 (16) | −0.0054 (15) |
C17 | 0.056 (2) | 0.036 (2) | 0.0312 (18) | −0.0137 (18) | 0.0114 (16) | −0.0051 (15) |
C18 | 0.054 (2) | 0.048 (2) | 0.038 (2) | −0.008 (2) | 0.0104 (17) | −0.0014 (17) |
C19 | 0.051 (2) | 0.057 (2) | 0.047 (2) | −0.009 (2) | 0.0170 (18) | −0.010 (2) |
C20 | 0.051 (2) | 0.068 (3) | 0.0306 (19) | −0.019 (2) | 0.0144 (16) | −0.007 (2) |
C21 | 0.079 (3) | 0.054 (3) | 0.032 (2) | −0.018 (2) | 0.0133 (19) | 0.0022 (18) |
C22 | 0.082 (3) | 0.040 (2) | 0.039 (2) | −0.006 (2) | 0.021 (2) | 0.0025 (17) |
O1—C9 | 1.363 (4) | C8—H8A | 0.9900 |
O1—C8 | 1.437 (4) | C8—H8B | 0.9900 |
O2—C15 | 1.237 (4) | C9—C14 | 1.382 (5) |
O3—N3 | 1.231 (6) | C9—C10 | 1.395 (5) |
O4—N3 | 1.227 (5) | C10—C11 | 1.373 (4) |
N1—C15 | 1.358 (4) | C10—H10 | 0.9500 |
N1—N2 | 1.376 (4) | C11—C12 | 1.395 (5) |
N1—H1 | 0.90 (4) | C11—H11 | 0.9500 |
N2—C16 | 1.279 (4) | C12—C13 | 1.396 (5) |
N3—C20 | 1.480 (5) | C12—C15 | 1.477 (4) |
C1—C2 | 1.511 (5) | C13—C14 | 1.379 (5) |
C1—H1A | 0.9800 | C13—H13 | 0.9500 |
C1—H1B | 0.9800 | C14—H14 | 0.9500 |
C1—H1C | 0.9800 | C16—C17 | 1.472 (5) |
C2—C3 | 1.353 (6) | C16—H16 | 0.9500 |
C2—C7 | 1.386 (5) | C17—C18 | 1.385 (5) |
C3—C4 | 1.379 (6) | C17—C22 | 1.398 (5) |
C3—H3 | 0.9500 | C18—C19 | 1.385 (5) |
C4—C5 | 1.381 (5) | C18—H18 | 0.9500 |
C4—H4 | 0.9500 | C19—C20 | 1.383 (6) |
C5—C6 | 1.352 (6) | C19—H19 | 0.9500 |
C5—C8 | 1.500 (5) | C20—C21 | 1.360 (6) |
C6—C7 | 1.377 (5) | C21—C22 | 1.374 (5) |
C6—H6 | 0.9500 | C21—H21 | 0.9500 |
C7—H7 | 0.9500 | C22—H22 | 0.9500 |
C9—O1—C8 | 117.8 (3) | C14—C9—C10 | 119.3 (3) |
C15—N1—N2 | 119.1 (3) | C11—C10—C9 | 119.5 (3) |
C15—N1—H1 | 124 (2) | C11—C10—H10 | 120.2 |
N2—N1—H1 | 117 (2) | C9—C10—H10 | 120.2 |
C16—N2—N1 | 116.0 (3) | C10—C11—C12 | 121.9 (3) |
O4—N3—O3 | 124.3 (4) | C10—C11—H11 | 119.1 |
O4—N3—C20 | 118.1 (4) | C12—C11—H11 | 119.1 |
O3—N3—C20 | 117.7 (4) | C11—C12—C13 | 117.9 (3) |
C2—C1—H1A | 109.5 | C11—C12—C15 | 118.8 (3) |
C2—C1—H1B | 109.5 | C13—C12—C15 | 123.3 (3) |
H1A—C1—H1B | 109.5 | C14—C13—C12 | 120.4 (3) |
C2—C1—H1C | 109.5 | C14—C13—H13 | 119.8 |
H1A—C1—H1C | 109.5 | C12—C13—H13 | 119.8 |
H1B—C1—H1C | 109.5 | C13—C14—C9 | 120.9 (3) |
C3—C2—C7 | 117.0 (4) | C13—C14—H14 | 119.5 |
C3—C2—C1 | 121.6 (4) | C9—C14—H14 | 119.5 |
C7—C2—C1 | 121.4 (4) | O2—C15—N1 | 122.1 (3) |
C2—C3—C4 | 121.8 (4) | O2—C15—C12 | 121.7 (3) |
C2—C3—H3 | 119.1 | N1—C15—C12 | 116.2 (3) |
C4—C3—H3 | 119.1 | N2—C16—C17 | 118.7 (3) |
C3—C4—C5 | 120.9 (4) | N2—C16—H16 | 120.6 |
C3—C4—H4 | 119.5 | C17—C16—H16 | 120.6 |
C5—C4—H4 | 119.5 | C18—C17—C22 | 119.3 (3) |
C6—C5—C4 | 117.6 (4) | C18—C17—C16 | 121.6 (3) |
C6—C5—C8 | 121.1 (3) | C22—C17—C16 | 119.1 (3) |
C4—C5—C8 | 121.2 (4) | C19—C18—C17 | 119.8 (4) |
C5—C6—C7 | 121.3 (4) | C19—C18—H18 | 120.1 |
C5—C6—H6 | 119.3 | C17—C18—H18 | 120.1 |
C7—C6—H6 | 119.3 | C20—C19—C18 | 118.6 (4) |
C6—C7—C2 | 121.4 (4) | C20—C19—H19 | 120.7 |
C6—C7—H7 | 119.3 | C18—C19—H19 | 120.7 |
C2—C7—H7 | 119.3 | C21—C20—C19 | 123.1 (3) |
O1—C8—C5 | 108.1 (3) | C21—C20—N3 | 118.5 (4) |
O1—C8—H8A | 110.1 | C19—C20—N3 | 118.4 (4) |
C5—C8—H8A | 110.1 | C20—C21—C22 | 117.9 (4) |
O1—C8—H8B | 110.1 | C20—C21—H21 | 121.1 |
C5—C8—H8B | 110.1 | C22—C21—H21 | 121.1 |
H8A—C8—H8B | 108.4 | C21—C22—C17 | 121.3 (4) |
O1—C9—C14 | 115.7 (3) | C21—C22—H22 | 119.3 |
O1—C9—C10 | 125.0 (3) | C17—C22—H22 | 119.3 |
C15—N1—N2—C16 | 166.0 (3) | C10—C9—C14—C13 | 2.9 (5) |
C7—C2—C3—C4 | 0.3 (7) | N2—N1—C15—O2 | −5.3 (5) |
C1—C2—C3—C4 | −179.5 (5) | N2—N1—C15—C12 | 174.1 (3) |
C2—C3—C4—C5 | −0.5 (8) | C11—C12—C15—O2 | −25.7 (5) |
C3—C4—C5—C6 | 0.2 (7) | C13—C12—C15—O2 | 151.0 (3) |
C3—C4—C5—C8 | 179.3 (4) | C11—C12—C15—N1 | 154.8 (3) |
C4—C5—C6—C7 | 0.2 (6) | C13—C12—C15—N1 | −28.5 (5) |
C8—C5—C6—C7 | −178.9 (4) | N1—N2—C16—C17 | −179.9 (3) |
C5—C6—C7—C2 | −0.4 (7) | N2—C16—C17—C18 | −27.8 (5) |
C3—C2—C7—C6 | 0.2 (7) | N2—C16—C17—C22 | 149.9 (4) |
C1—C2—C7—C6 | 179.9 (4) | C22—C17—C18—C19 | −0.4 (5) |
C9—O1—C8—C5 | −170.9 (3) | C16—C17—C18—C19 | 177.2 (4) |
C6—C5—C8—O1 | 80.9 (4) | C17—C18—C19—C20 | −0.6 (5) |
C4—C5—C8—O1 | −98.2 (5) | C18—C19—C20—C21 | 0.5 (6) |
C8—O1—C9—C14 | 177.9 (3) | C18—C19—C20—N3 | 179.1 (4) |
C8—O1—C9—C10 | −3.5 (5) | O4—N3—C20—C21 | 1.5 (5) |
O1—C9—C10—C11 | 179.5 (3) | O3—N3—C20—C21 | −177.5 (4) |
C14—C9—C10—C11 | −2.0 (5) | O4—N3—C20—C19 | −177.2 (4) |
C9—C10—C11—C12 | 0.0 (5) | O3—N3—C20—C19 | 3.9 (5) |
C10—C11—C12—C13 | 1.1 (5) | C19—C20—C21—C22 | 0.7 (6) |
C10—C11—C12—C15 | 177.9 (3) | N3—C20—C21—C22 | −177.9 (3) |
C11—C12—C13—C14 | −0.2 (5) | C20—C21—C22—C17 | −1.8 (6) |
C15—C12—C13—C14 | −176.9 (3) | C18—C17—C22—C21 | 1.7 (6) |
C12—C13—C14—C9 | −1.8 (5) | C16—C17—C22—C21 | −176.0 (3) |
O1—C9—C14—C13 | −178.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N2i | 0.95 | 2.68 | 3.524 (5) | 148 |
C16—H16···O2ii | 0.95 | 2.45 | 3.259 (4) | 143 |
C21—H21···O4iii | 0.95 | 2.59 | 3.532 (5) | 171 |
N1—H1···O2ii | 0.90 (4) | 2.04 (4) | 2.911 (4) | 161 (3) |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z. |
Acknowledgements
The authors express their gratitude to the Department of Chemistry, University of Rajshahi for laboratory facilities. MCS and RM acknowledge the Center for Environmental Conservation and Research Safety, University of Toyama for providing facilities for single-crystal X-ray analyses.
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